This invention relates to the cephalosporin class of antibiotics. In particular, this invention relates to a process for preparing 3-hydroxymethyl-2-cephem compounds and to certain cephem ester intermediates therein.
3-Hydroxymethylcephems are known in the cephalosporin art and have proved to be useful intermediates for the preparation of many related cephalosporin antibiotic compounds. Heretofore 3-hydroxymethylcephems have been generally available by chemical or enzymatic deesterification procedures from the corresponding 3-acetoxymethylcephems (derivatives of cephalosporin C). Thus a 7-acylamino-3-acetoxymethyl-3-cephem-4-carboxylic acid can be treated with an esterase derived from Bacillus subtilis or with orange peel esterase to form the corresponding 7-acylamino-3-hydroxymethyl-3-cephem-4-carboxylic acid. The preparation and recognized utility of 3-hydroxymethylcephems, products of the process of the present invention, has been disclosed generally in U.S. Pat. Nos. 3,196,151, issued July 20, 1965; 3,218,318, issued Nov. 16, 1965; 3,436,310, issued Apr. 1, 1969; and 3,459,746, issued Aug. 5, 1969.